Financial support was provided by the National Natural Science Foundation of China (21032003, 20921092 and 21125208) and the National Basic Research Program of China (2010CB833300).
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Communication
Iridium-Catalyzed Asymmetric Hydrogenation of Pyridinium Salts†
Article first published online: 11 SEP 2012
DOI: 10.1002/anie.201205187
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
1521-3773/asset/cover.gif?v=1&s=412bc65bdcb3f0e34a94f27c1c13e908726694d4 "Angewandte Chemie International Edition")
Angewandte Chemie International Edition
Volume 51, Issue 40, pages 10181–10184, October 1, 2012
Additional Information
How to Cite
Ye, Z.-S., Chen, M.-W., Chen, Q.-A., Shi, L., Duan, Y. and Zhou, Y.-G. (2012), Iridium-Catalyzed Asymmetric Hydrogenation of Pyridinium Salts . Angew. Chem. Int. Ed., 51: 10181–10184. doi: 10.1002/anie.201205187
- †
Publication History
- Issue published online: 26 SEP 2012
- Article first published online: 11 SEP 2012
- Manuscript Received: 2 JUL 2012
Funded by
- National Natural Science Foundation of China. Grant Numbers: 21032003, 20921092, 21125208
- National Basic Research Program of China. Grant Number: 2010CB833300
Keywords:
- asymmetric synthesis;
- hydrogenation;
- iridium;
- piperidines;
- pyridines
Highly efficient iridium-catalyzed asymmetric hydrogenations of simple 2-substituted pyridinium salts gives the chiral 2-substituted piperidines with up to 93 % ee (see picture; cod=1,5-cyclooctadiene; synphos=(5,6),(5′,6′)-bis(ethylenedioxy)-2,2′-bis(diphenylphosphino)-1,1′-biphenyl). The key feature of this strategy is the activation of simple pyridines as the pyridinium salts, thus eliminating substrate inhibition and enhancing the reactivity.